Aminosubstituted arylpyrazolon.



f Wr n WALTER KRQPP, 0E ELBERFELD, GEENIANY, ASSIGNOF. TO SYIII'TT-IETIC PATENTS CCL,

ENC NE'W $393K, N. Y., A CORPORATION GE NEW YGRK.

AMINGSUBSTITUTED AEYLPYRAZGLDN.

To (all Q07 am it may; 07166771,

it imown that l WAL'rnn Kuorr, doctor of philosophy, chemist, citizen ()1 the German Empire, residing at lllheri'eld, Germany, have invented new and useful Inn provements in Aininosuhstituted iirylpyrazolons, of which the following is a specification.

l have found that aminosuhstituted arylpyrazolons can he condensed with the acidylized pyruvic acid compounds 6. g.

cuncocniccoon I co N-C5H5 CH3.CO.CH7,.C.COOH

CH: 6:; cnsq 0 f These products have proved to he valuable antipyretics and antineuralgics, an average single dose being from 1 to 2 grams. The new products are generally yellowish crystalline compounds soluble with diiii culty in water and organic solvents, but easily soluble in alkalis. They form salts such as sodium, potassium, calcium and quinin salts, which retain the valuable therapeutic properties of the free compounds.

In order to illustrate the new process more fully the following example is given, the p is being by weight-2000 parts of normal caustic soda lye are poured over 360 parts of the sodium salt of acetylpyruvic acid ester (acetone oxalic acid ester if -CO-Cll,-CO-C0OC H and are allowed to stand until a test portion does no more give a yellowish oily precipitate when acidulated with acetic acid. 400 parts oil? l-phenyl-Qfl-niinethyl--amino-5-pyrazolon are then added to it and acidulated with hydrochloric acid. After live minutes the Specification of Letters Eetent.

Application filed May 23, 1914.

Serial No. 840,5Q4i.

The sodium salt of this product can be cl t ained by adding an alcoholic solution of sodium ethylate to th 5 acid and distilling oil the alcohol. The c lciuni salt of this acid is produced laysuing calcium carbonate to the aqueous suspension of the acid. ll hen the carbonic acid is escaped it is iiltel-ed oil and the is evaporated in cacao. The neutral thus separated is washed with. alcohol and ether.

In an manner other of the above mentioned acids are obtained the condensation product of henzoylpyruvic acid and 1-phenyl-2.3--dimethyld-arnino-5- pyrazolon, crystalline substance melting at about 195 C., the quinin selt melting at 210 C., the condensation product of acetylpyruvic acid with Lmetatolyl-Q.S-dimethyl- 4i-:unino--pyrazolon melting at about 1'Z5 (1., etc.

1. The new condensation products of arylaminopyrazolons and acidylpyruvic acid compounds which are generally yellowish crystalline compounds soluble with difiiculty in water and organic solvents, easily soluble in alkalis, fox-tiling salts and being valuable antipyretics end antine ralgics, substantially as described.

2. The new condensation products phenylaininopyrazoions and acidylpyruvic acid compounds which are generally yellowish crystalline compounds soluble with di'liiculty in water and organic solvents, easily soluble in allialis, forming salts and being valuable antipyrctics and antineuralgics, suhstantially as described.

1-3. The new condensation products of arylaminopyrazolons and acetylpyruvic acid compounds which. are generally yellowish crystalline compounds soluble with dilliculty in Water and organic solvents, easily soluble in alkalis, forming salts and being valuable antipyretics and antineuralgics, substantially as described.

4. The new condensation products of phenylaminopyrazolons and acetylpyruvic acid compounds Which are generally yellowish crystalline compounds soluble With difficulty in water and. organic solvents, easily soluble in alkalis, forming salts and being valuable antipyretics and antineuralgics, substantially as described.

5. The new condensation products of 1- aryl-2.3-dimethyll-amino-5-pyrazolons and acidylpyruvic acid compounds Which are generally yellowish crystalline compounds soluble with difliculty in Water and organic solvents, easily soluble in alkalis, forming salts and being valuable antipyretics and antineuralgics, substantially as described.

6. The new condensation products of 1- aryl-QB-dimethyl-t-amino-5-pyrazolons and acetylpyruvic acid compounds Which are generally yellowish crystalline compounds soluble With ditficulty in Water'and organic solvents, easily soluble in alkalis, forming salts and being valuable antipyretics and antineuralgics, substantially as described.

7. The neW condensation products of 1-phenyl-2.3-dimethyl--amino-5-pyrazolons and acidylpyruvic acid compounds which are generally yellowish crystalline compounds soluble with ditficulty in Water and organic solvents, easily soluble in alkalis, forming salts and being valuable antipyreticsand antineuralgics, substantially as described.

8. The new condensation product obtained from acetylpyruvic acid and 1-phenyl-2.3- dimethyl-4-amino5-pyrazolon having most probablythe following formula:

pyretic and antineuralgic, substantially as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing Witnesses.

WALTER KROPP. [1 s] Nitnesses HELEN NUFER, FRANCES NUFER. 

